3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde | 1383551-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde
• 英文别名: 3-(2-Benzothiazolyl)-2-hydroxy-1-naphthalenecarboxaldehyde
• CAS: 1383551-42-5
• 化学式: C₁₈H₁₁NO₂S
• 分子量: 305.357
• InChiKey: BAYSMYGBRRNWQS-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  511.2±60.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以64%的产率得到1,1'-((1E,1'E)-hydrazine-1,2-diylidenebis(methanylylidene))bis(3-(benzo[d]thiazol-2-yl)naphthalen-2-ol)
  参考文献：
  名称：

  Pigment Yellow 101 analogs from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde – Synthesis and characterization

  摘要：

  Pigment Yellow 101 analogs have been synthesized from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde by combining with different aromatic diamines. Out of the four synthesized aldazines two show pigment properties and remaining show properties like dyes. Existence of excited state intramolecular proton transfer process between phenolic OH and azomethine linkage (=N-) has been computationally ascertained. Two pigment analogs showed solid state fluorescent which were compared with commercially available Pigment Yellow 101. For dyes analogs, effects of solvent polarity on photophysical properties such as absorption, emission have been studied. Density functional theory and time dependent density functional theory computations have been used to investigate structural parameters and understanding photophysical properties of synthesized analogs. All these aldazines show good thermal stability. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.08.015
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 sodium hydroxide 、 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde
  参考文献：
  名称：

  Photophysical properties of Schiff’s bases from 3-(1,3-benzothiazol-2-yl)-2-hydroxy naphthalene-1-carbaldehyde

  摘要：

  A series of novel Schiff's bases have been synthesized from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde. The presence of hydroxyl group ortho to the benzothiazolyl group as well as the imine linkage lead to the occurrence of excited state intramolecular proton transfer process. The computational strategy was used to study the ESIPT process of the synthesized Schiff's bases, which revealed surprisingly that the keto form predominantly exists in the ground state contradicting the ESIPT process. Density functional theory and time dependent density functional theory have been used to investigate the structural parameters and photophysical properties in different solvents of one of the Schiff's bases. The experimental results correlate well with the computed results. All Schiff's bases show good thermal stability.

  DOI：

  10.1016/j.saa.2014.05.029

文献信息

• Spiropyrans and spirooxazines 8. 5′-(1,3-Benzothiazol-2-yl)-substituted spiro[indoline-2,3′-naphthopyrans]: synthesis and spectral and photochromic properties
  作者：N. A. Voloshin、A. V. Chernyshev、A. V. Metelitsa、E. B. Gaeva、V. I. Minkin

  DOI：10.1007/s11172-011-0289-2

  日期：2011.9

  Novel photochromic 5′-(1,3-benzothiazol-2-yl)-substituted spiro[indoline-2,3′-naphthopyrans] possessing luminescence properties in both the cyclic and merocyanine forms were synthesized. Unlike the 8′-(1,3-benzothiazol-2-yl)-substituted benzopyran analogs, the synthesized compounds are characterized by the lower relative stability of the merocyanine isomers.

  合成了新型光致变色的 5′-(1,3-苯并噻唑-2-基)取代螺[吲哚啉-2,3′-萘并吡喃]，其环状和经花青素形式均具有发光特性。与 8′-(1,3-苯并噻唑-2-基)取代的苯并吡喃类似物不同，所合成的化合物的特点是经花青素异构体的相对稳定性较低。
• A combined theoretical and experimental investigation on the solvatochromism of ESIPT3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde
  作者：Manjaree A. Satam、Rahul D. Telore、Abhinav B. Tathe、Vinod D. Gupta、Nagaiyan Sekar

  DOI：10.1016/j.saa.2014.01.120

  日期：2014.6

  Excited state intramolecular proton transfer inspired 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde, showing solid state fluorescence has been synthesized. Existence of excited state intramolecular proton transfer process between carbonyl group and phenolic -OH group has been theoretically predicted using computational method. Density functional theory and time dependent density functional theory computations have been used to investigate structural parameters and understand the photophysical properties of the synthesized carbaldehyde. The photophysical properties of carbaldehyde were evaluated using UV-Visible and fluorescence spectroscopy and are found to be very sensitive to the microenvironment such as solvent polarity and pH. The experimental absorption-emission a results are correlated with the computed values. The increase in the dipole moment of A2-Keto* than A2-Enol* suggested the presence of keto form in the excited state and which is responsible for the single fluorescence emission with a large Stokes shift in all solvents. (C) 2014 Elsevier B.V. All rights reserved.
• Novel Photo- and Ionochromic Benzothiazole-Substituted Spirobipyrans
  作者：E. V. Solov’eva、N. A. Voloshin、A. V. Chernyshev、Yu. S. Reutova、A. V. Metelitsa

  DOI：10.1134/s0012500820090050

  日期：2020.9

  Novel photochromic spirobipyrans containing benzothiazole group in the 2H-chromene moiety have been synthesized. The spirobipyrans combine with Co2+, Ni2+, Zn2+, and Cu2+ ions to give intensely colored complexes of merocyanine form with long-wavelength absorption bands at lambda > 600 nm.
• US4256900A
  申请人：——

  公开号：US4256900A

  公开（公告）日：1981-03-17
• Photophysical properties of Schiff’s bases from 3-(1,3-benzothiazol-2-yl)-2-hydroxy naphthalene-1-carbaldehyde
  作者：Manjaree A. Satam、Rahul D. Telore、Nagaiyan Sekar

  DOI：10.1016/j.saa.2014.05.029

  日期：2014.11

  A series of novel Schiff's bases have been synthesized from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde. The presence of hydroxyl group ortho to the benzothiazolyl group as well as the imine linkage lead to the occurrence of excited state intramolecular proton transfer process. The computational strategy was used to study the ESIPT process of the synthesized Schiff's bases, which revealed surprisingly that the keto form predominantly exists in the ground state contradicting the ESIPT process. Density functional theory and time dependent density functional theory have been used to investigate the structural parameters and photophysical properties in different solvents of one of the Schiff's bases. The experimental results correlate well with the computed results. All Schiff's bases show good thermal stability.